Boro rice (Oryza sativa L.) plays a crucial role in ensuring food security in Bangladesh, yet its productivity is challenged by recurring insect pest and disease outbreaks. This study analyzed 5 years (2019–2023) of data to assess the temporal patterns of insect pest and disease outbreaks in Boro rice cultivation in Bangladesh and evaluate the effectiveness of pesticide and non-pesticide control strategies. Results showed that insect pests consistently affected larger areas than diseases, with April being the most vulnerable month. Insect pest management remained moderately balanced between chemical and eco-friendly approaches, while disease control exhibited a significant shift toward non-pesticide methods reaching nearly 90% nonchemical coverage by 2023. Protection rates for both pest types followed a U-shaped trend across years, with the lowest efficacy observed in 2022 and highest in 2020 and 2023. A significant negative correlation (r = −0.45, p < 0.05) was found between insect-affected land and protection rate, suggesting reduced effectiveness during larger outbreaks. These findings highlight the importance of pest-specific and time-sensitive strategies, as well as the growing role of sustainable management practices in ensuring the resilience of rice production systems.